Compound, organic light-emitting device and display device

Abstract

Provided, according to the present invention, are a compound which may be applied to an electron transport layer of an organic light-emitting device, an organic light-emitting device using such compound and an organic EL display device comprising such organic light-emitting device.

Description

technical field

[0001] The invention relates to a compound, an organic light-emitting device and an organic EL display device. Background technique

[0002] In general, the organic light-emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic light emitting device using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, the organic material layer generally has a multilayer structure composed of multiple layers of different materials to increase the efficiency and stability of the organic light emitting device, for example, the organic material layer can be composed of a hole injection layer, a hole transport layer, a light emitting layer, Electron transport layer, electron injection layer and other components.

[0003] In the above-mentioned structure of the organic light-emitting device, w...

Examples

Synthetic example

[0284] Synthesis Example (Compounds 1-1-1 to 1-1-3)

[0285] After dissolving 2-(benzo[kl]thioxanth-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (20 g, 55.5 mmol) in THF , add 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (20.9g, 61.1mmol), Pd(PPh 3 ) 4 (2g, 1.7mmol), NaOH (6.8g, 168.9mmol) and water, and then stirred under reflux at 100°C for 3 hours. When the reaction is over, extract with E.A and water, and wash the organic layer with MgSO 4 After drying and concentration, the resulting organic matter was passed through a silica gel column followed by recrystallization, thereby obtaining 20 g of a final product (yield: 67%).

[0286]

[0287] Compounds 1-1-2 to 1-1-3 can be synthesized in the same method as that of Compound 1-1-1 by using Cores 1-2 to 1-3.

[0288] Synthesis Example (Compounds 1-2-1 to 1-2-3)

[0289] After dissolving 2-(benzo[kl]thioxanth-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (20 g, 55.5 mmol) in THF , added 2-([1,1'-biphenyl]-4-y...

Embodiment

[0552] Example (compound 31-3-9)

[0553] 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[4,5]thiochromene[2,3-b]pyridine ( 20g, 55.4mmol) was dissolved in THF, and 1-bromo-4-iodobenzene (17.2g, 60.9mmol), Pd(PPh 3 ) 4 (2g, 1.7mmol), NaOH (6.6g, 166.2mmol) and water, and then stirred under reflux at 100°C for 3 hours. When the reaction is over, extract with E.A and water, and wash the organic layer with MgSO 4 Drying and concentration, then recrystallization after the organic matter that generates is passed through silica gel column, thereby obtain the intermediate product of 15.4g namely 1-(4-bromobenzene) benzo [4,5] thiochromene [2,3-b ] Pyridine.

[0554] After dissolving 1-(4-bromobenzene)benzo[4,5]thiochromene[2,3-b]pyridine (15.4 g, 39.3 mmol) as an intermediate in DMF in a round-bottomed flask, add bis Pinacol borate (11g, 43.2mmol), Pd(dppf)Cl 2 (0.9g, 1.2mmol) and KOAc (16.3g, 117.9mmol), and then stirred under reflux at 130°C for 4 hours. When the reacti...

Embodiment 1～38

[0570] Embodiments 1-38 (Application Examples in Electron Transport Layers of Blue Organic Light-Emitting Devices)

[0571] Corning (corning) 15Ω / cm 2 The ITO glass substrate was immersed in distilled water in which a dispersant was dissolved to be cleaned with ultrasonic waves. The detergent used here was a product purchased from Fischer Co., and the distilled water was distilled water filtered twice using a filter (Filter) purchased from Millipore Co. The ITO was washed for 30 min, followed by two repetitions of ultrasonic washing with distilled water for 10 min. After washing with distilled water, it was followed by ultrasonic washing with isopropanol, acetone, and methanol solvents in sequence, and dried.

[0572] A hole-injection layer with a thickness of 60 nm was formed by vacuum-depositing 2-TNATA on the ITO anode layer, and then vacuum-deposited 4,4-bis[N-(1-naphthyl)-N-benzene on the above-mentioned hole-injection layer Amino]biphenyl (hereinafter referred to as...

technical field

[0001] The invention relates to a compound, an organic light-emitting device and an organic EL display device. Background technique

[0002] In general, the organic light-emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic light emitting device using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, the organic material layer generally has a multilayer structure composed of multiple layers of different materials to increase the efficiency and stability of the organic light emitting device, for example, the organic material layer can be composed of a hole injection layer, a hole transport layer, a light emitting layer, Electron transport layer, electron injection layer and other components.

[0003] In the above-mentioned structure of the organic light-emitting device, w...

Examples

Synthetic example

[0284] Synthesis Example (Compounds 1-1-1 to 1-1-3)

[0285] After dissolving 2-(benzo[kl]thioxanth-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (20 g, 55.5 mmol) in THF , add 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (20.9g, 61.1mmol), Pd(PPh 3 ) 4 (2g, 1.7mmol), NaOH (6.8g, 168.9mmol) and water, and then stirred under reflux at 100°C for 3 hours. When the reaction is over, extract with E.A and water, and wash the organic layer with MgSO 4 After drying and concentration, the resulting organic matter was passed through a silica gel column followed by recrystallization, thereby obtaining 20 g of a final product (yield: 67%).

[0286]

[0287] Compounds 1-1-2 to 1-1-3 can be synthesized in the same method as that of Compound 1-1-1 by using Cores 1-2 to 1-3.

[0288] Synthesis Example (Compounds 1-2-1 to 1-2-3)

[0289] After dissolving 2-(benzo[kl]thioxanth-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (20 g, 55.5 mmol) in THF , added 2-([1,1'-biphenyl]-4-y...

Embodiment

[0552] Example (compound 31-3-9)

[0553] 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[4,5]thiochromene[2,3-b]pyridine ( 20g, 55.4mmol) was dissolved in THF, and 1-bromo-4-iodobenzene (17.2g, 60.9mmol), Pd(PPh 3 ) 4 (2g, 1.7mmol), NaOH (6.6g, 166.2mmol) and water, and then stirred under reflux at 100°C for 3 hours. When the reaction is over, extract with E.A and water, and wash the organic layer with MgSO 4 Drying and concentration, then recrystallization after the organic matter that generates is passed through silica gel column, thereby obtain the intermediate product of 15.4g namely 1-(4-bromobenzene) benzo [4,5] thiochromene [2,3-b ] Pyridine.

[0554] After dissolving 1-(4-bromobenzene)benzo[4,5]thiochromene[2,3-b]pyridine (15.4 g, 39.3 mmol) as an intermediate in DMF in a round-bottomed flask, add bis Pinacol borate (11g, 43.2mmol), Pd(dppf)Cl 2 (0.9g, 1.2mmol) and KOAc (16.3g, 117.9mmol), and then stirred under reflux at 130°C for 4 hours. When the reacti...

Embodiment 1～38

[0570] Embodiments 1-38 (Application Examples in Electron Transport Layers of Blue Organic Light-Emitting Devices)

[0571] Corning (corning) 15Ω / cm 2 The ITO glass substrate was immersed in distilled water in which a dispersant was dissolved to be cleaned with ultrasonic waves. The detergent used here was a product purchased from Fischer Co., and the distilled water was distilled water filtered twice using a filter (Filter) purchased from Millipore Co. The ITO was washed for 30 min, followed by two repetitions of ultrasonic washing with distilled water for 10 min. After washing with distilled water, it was followed by ultrasonic washing with isopropanol, acetone, and methanol solvents in sequence, and dried.

[0572] A hole-injection layer with a thickness of 60 nm was formed by vacuum-depositing 2-TNATA on the ITO anode layer, and then vacuum-deposited 4,4-bis[N-(1-naphthyl)-N-benzene on the above-mentioned hole-injection layer Amino]biphenyl (hereinafter referred to as...

Images